Methyl iodide → methyl (2S)-3-hydroxy-2-(methyl(p-tolylsulfonyl)amino)propanoate

HRID 1479816노트

반응식

HRID 1479816 반응식
[OH:1][CH2:2][C@H:3]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4]([O:6][CH3:7])=[O:5].[C:19]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[OH:1][CH2:2][C@H:3]([N:8]([CH3:19])[S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:4]([O:6][CH3:7])=[O:5]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6928423(S)-methyl 3-hydroxy-2-(4-methylphenylsulfonamido)propanoate

생성물 1

HCID 131736587methyl (2S)-3-hydroxy-2-(methyl(p-tolylsulfonyl)amino)propanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

A solution of 2E (2 g, 7.35 mmol) in DMF (15 mL) was added with an .K2CO3 (1.5 mol eq, 1.52 g) and, after few minutes, iodomethane (1.2 mol eq, 0.81 ml) was added and the mixture was heated at 50° C. overnight. The solvent was removed under reduced pressure, water was added to the residue (120 mL) and the aqueous phase was extracted with EtOAc (3×50 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 3E as a pale yellow oil (2.1 g, quantitative yield). 1HNMR (DMSO, 200 MHz) δ 2.38 (s, 3H), 2.87 (s, 3H), 3.64 (s, 3H), 3.70 (t, 2H), 4.58 (t, 1H), 5.11 (t, 1H), 7.40 (d, 2H, J=8), 7.61 (d, 2H, J=8).

후처리

  1. customThe solvent was removed under reduced pressure, water
  2. additionwas added to the residue (120 mL)
  3. extractionthe aqueous phase was extracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-088194fb56c64339bc0f4c99852f3336
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409864B2

반응 노트

불러오는 중…